Hell's Prison
by lindsayd16
Summary: When Dean wakes up and finds himself locked away in Hell's Prison, he looks to new friends and his brother to get him out. Takes place around season two, details altered. Rated T for language.
1. Chapter 1

**Author's Note: I'm basically simplifying the Winchester's lives. I'm not including the fact that the Apocalypse happened or that they were Archangels vessels. If anything, this would be set in roughly season two. They don't know anything about angels (yet). Carry on.**

**CHAPTER ONE: Unexpected Turn Of Events**

It was a routine hunt.

Quick and easy, exorcize and go.

But, when were things ever easy in my life?

I had first caught wind of this particular demon when I was visiting Bobby. He had told me of a string of murders that resembled crossroad deals.

A little more research and I was off, just itching to gank some punk ass crossroad demon.

"Dean, maybe you should call Sam. You could always use the help." Bobby had told me right before I left.

"Sammy doesn't want anything to do with me or this. I'll pass." I said, waving off his dumbass suggestion.

To clarify, I was just protecting my brother. We were on a simple case, another demon. Except this demon was the one who had killed our mother.

Our dad had gotten possessed by the yellow-eyed dick, ambushed us with our pants down, and came pretty damn close to killing Sam.

I saw my opening, took the colt, and shot our father through the heart, killing the demon and him.

Sam never was able to forgive me after that. But it had to be done and I have a gut feeling my dad would've been proud of me.

Anyways, Sam had left shortly after that claiming he couldn't even look at me anymore.

So I continued to hunt.

As I drove to some hick town down in Alabama, I found myself thinking about the second cell phone I had that was stashed in the Impala's glove compartment.

Stopping for gas, I dug the phone out and turned it on. I scrolled down to the one of three contacts in the phone that had Sam's number and almost called him.

But I guess I wasn't really in the mood to get yelled at because I snapped the phone shut quickly, shoving it back deep into its storage place.

It was about a twenty hour drive which I made without stopping.

Finally stopping at a motel, I barely made it in the room before I collapsed on the bed and passed out.

….

I was woken up by the thin ray of light that was slicing through the darkness from the gap in the curtains. Rolling onto my back, I rubbed the sleep from my eyes before I glanced at the clock. _Fucking nine am already._

Hauling my ass out of bed, I made my way to the bathroom to shower and piss.

After taking my time, I was finally ready to head out and kill some evil son of bitch.

….

_Dark alleys give me the fucking creeps._ I thought as I made my way down the narrow pathway. Taking my gun's safety off, I held it out in front of me.

A noise coming from behind a dumpster up ahead caused my pace to quicken and my senses to heighten. I had been hunting for just about my whole life and enjoyed the feel of adrenaline pumping through my veins.

Moving along the edge of the dumpster, I quickly maneuvered so I was facing behind it only to see a rat scurrying away.

"Disgusting." I muttered.

"I agree." A smug voice said from behind me.

Spinning around, I pointed my gun at the black eyed stranger. "Huh, this whole time I've been looking for you. I didn't think you'd come to me." I said, smirking as I put my gun in my waist band and took out the demon killing knife that had been in my family for years.

"Now, where did you get that?" The demon in front of me had possessed some poor banker by the looks of the cheap suit.

"Pulled it out of my ass a week ago. Call off all the deals you've got going." I ordered, twirling the blade in my hand.

"Dean Winchester. You sure live up to your reputation. A smart ass and stupid. There are no deals going down here genius. We were just trying to get your attention." With a flick of his wrist, he pinned me up against the brick wall.

Grimacing, I gripped the knife and glared at my attacker. "Well here I am. What do you want?" I spat.

"We're under strict orders to capture and bring you down to the furnace. The King doesn't like all you've done to his men." The demon strolled over to me, taking out a wickedly sharp knife from his jacket pocket. Running it along my jaw line, he grabbed my wrist and pressed hard down on the vein, causing me to let the knife fall to the asphalt.

I chuckled humorlessly as I stared the demon down. "Listen here you black-eyed dick, if you're King has a problem with me, tell him to grow some balls and come topside and deal with me himself."

"See that's not nearly as much fun."

The last thing I remember is a blinding pain to my temple and everything going dark.

….

I woke up with a bitch of a headache. Feeling something drip down my cheek, I went to wipe it off when I felt my wrists were bound.

My eyes flew open as I glanced down to see my wrists were clamped together with chains that wrapped around the leg of the cot I was laying flat on my stomach on.

"What the fuck…" I said, glancing around the room to take in my surroundings.

The walls and flooring were black with blood stains spaced sporadically around almost every inch of the small space.

It was set up like a prison cell, bars in all separating me from the hallway with more cells on the opposite side. Looking down, I noticed I had been stripped down to just my black t-shirt, jeans, and boots.

Getting up, I moved as far as I could away from the bed which was a solid three feet before I felt resistance.

"Hey! Where am I?!" I called down the long dark hallway. The only source of lighting was the occasional lit torch on the hallway walls.

"Buddy, it's useless. The guards just left, they won't be back for another two hours." A gruff voice with a bit of an accent drawled from the cell opposite of me.

"Who are you? Where am I?" I asked again to the stranger. I watched as he stood up and made his way over to the bars. His wrists weren't bound like mine and he gripped the bars with both hands.

"Welcome to Hell's Prison. I'm Benny."

….

**TBC**

**Please leave reviews and let me know if I should continue or not. Thanks for reading.**


	2. Chapter 2: The Fun Begins

**CHAPTER TWO: The Fun Begins**

"I'm sorry, Hell's what?" I asked in disbelief.

Benny rolled his eyes. "Hell's Prison. Only the people who really piss off the King get sent down here. You're in the deepest darkest pit Hell has."

"Uh-huh." I said skeptically."So what did you do? Are you another hunter?" I questioned.

"Something like that." Benny chuckled as he beckoned me forward with his hand. Yanking on the chains, I got as close to the bars as I could. Taking one of his hands, he pulled up his lips revealing rows of sharp vampire fangs.

"Great, my first friend is some blood-sucking leach." I quipped. Obviously offended at my comment, Benny hissed and banged on the bars. "I suggest you keep your stereotypes to yourself, boy. The more friends you have here the better." He paused for a second as I put my arms up the best I could as an act of surrender. "You got a name, hunter?"

"Winchester." I said flatly.

"No, you gotta be kiddin' me. Not _Dean _Winchester?" He asked, trying to hide his amusement.

"What's it to you?" I snapped. Who the fuck did this guy think he was?

"I'm sorry." He said through fits of chuckles. "It's just that I heard stories about you. None of them talked about you bein' easy to catch though."

I rolled my eyes as I plopped down on the stiff cot. Groaning, I turned my head to face the vampire. "Call it a moment of weakness. I was ambushed. At least ten of em." It was almost funny how easy lies rolled off my tongue.

"Whatever gets you through the night Dean-o." Benny said, by his tone I could tell he didn't believe me.

"Would you two morons shut the fuck up." A gravelly voice from the cell next to Benny hissed.

"Don't mind him. Cas here just gets testy when he doesn't get his beauty rest." Benny said, sending a disapproving glare at the wall separating the two.

"You're just bitter that nothing can help that ass you call a face." Cas said, shuffling over to the bars. "Dean Winchester in the flesh. What a disappointment you are." As the irritable stranger made his way in the light, I wasn't able to tell if he was human or not. He had dark tousled hair and was wearing what resembled a dress shirt and torn slacks.

"You don't know shit about me." I spat. Were all the people down here dicks?

"Alright. You're wrong but, okay." Cas said, a smirk evident in his voice.

"Who the fuck are you anyways? Another vamp?" I asked.

"Don't call me one of those bottom-feeders." Cas hissed.

"Hey!" Benny said, obviously hurt by the comment.

"No offense." Cas said too sweetly. "I'm an angel you ass."

I couldn't help the laughter that erupted from my mouth. Noticing his deadly serious face, my laughter wound down to chuckles and then nothing.

"You're shitting me. Angels aren't real." I said incredulously.

Cas rolled his eyes and he returned to his cot, the bed springs squeaking under his weight. "There's a whole world out there you don't know about Dean. Try not to sound incompetent when you claim things aren't real that really are."

Before the conversation could continue, a door at the end of the rows of cells creaked open slowly, light flooding in.

"Uh-oh." Benny said, whistling.

"What? Why 'uh-oh'? I asked, my heart rate increasing.

"She's starting early today. Probably with you too." Cas said from his relaxed position on his bed.

"Who? Dammit, stop with these vague answers." I said through clenched teeth.

"Ruby." Was all Benny said.

….

"Hello boys." Ruby said seductively as she made her way in front of Cas's cell. "Castiel, looking ravishing as always this morning."

Cas groaned in response as she moved to Benny's cell. "You on the other hand, well, you tried." After a growl from the vampire, Ruby sent him a wink before turning around to look at me with black eyes. The girl she was possessing was slim and blonde and probably the type of girl I would've gone after in a bar.

"Dean Winchester. I can't tell you how long I've been waiting for this." She smiled smugly as she rested her arms on the horizontal bars.

"Last time someone looked at me like that, I got laid." I quipped.

She laughed slightly as she pulled out a ring of keys from her back pocket. "I think I'll start with Mr. Smart Ass today." With a sly grin, she flipped to the right key and pushed it into the key hole.

With a loud click, the door opened slowly as Ruby made her way over to me.

"Start with what?" I said as she undid the chains around the cot leg and gripped a hold of them.

A cruel smile crept across her face as she tugged on the chains, dragging me after her. "I don't want to ruin the surprise."

As we made our way down the hallway I could hear comments coming from the onlookers. Some whistled while other's made crude comments.

"Careful with his pretty face, Ruby." I heard Cas say sarcastically.

"Good luck, man." Benny had whispered encouragingly.

"Smack that ass kid, smack that ass." Some other jackass said from somewhere in the middle.

Opening the door, Ruby shoved me through it and slammed it shut behind her, cutting off all the whooping and hollering.

Leading me down more sets of hallways, we finally stopped outside a room with the door handle covered in blood.

Once inside, my stomach was in my throat.

The room would've resembled a surgical wing besides the fact that it was splattered with crimson from floor to ceiling with one long table with different restraints attached to it in the middle. A rack of different knives, bottles, and syringes wrapped all the way around the room.

Before I had time to take in the rest of my surroundings, Ruby injected something into my neck.

….

**TBC**

**Please continue to read and review. They mean a lot to me and let me know if I should continue with the story!**


	3. Chapter 3: Sticks and Stones

**CHAPTER THREE: Sticks And Stones**

When my eyes lazily opened, I couldn't make out any details in my surroundings because my vision was so fucking blurry.

Yanking half-heartedly on the tight restraints around my wrist and ankles, I glared up at Ruby. "What the fuck? Did you ruffie me?"

Ruby was on the opposite side of the room, huddled over a cart. "Something like that." I could hear the smugness in her voice as she turned around holding a wickedly sharp knife, making her way over to me.

My vision was starting to clear up and the jagged edges of the blade now looked even worse. "Woah maybe we can talk about this." I suggested.

"Sure, let's talk." With that, she sliced the knife across my now bare torso leaving a cut that extended from just below my right armpit to my left hip.

It took all I had to keep from screaming. But after being a hunter for so long, I was used to some pain.

"Now," She paused as she shoved the blade through my thigh and left it there. This time I couldn't help it. I let out a small pained scream eliciting a sly grin to cross Ruby's face. "Let's talk about why you're here."

"About fucking time. The suspense has been killing me." I said, my voice laced with pain and sarcasm.

Gripping a hold of the blade jammed in my thigh, she twisted it 180 degrees. I let out a groan while she continued.

Son of a bitch." I spat.

"See, you've really pissed off the King."

"Is that so? Well, I haven't had a visit from him yet." I quipped.

"Don't interrupt me!" She yelled as she twisted again. She took a deep breath to calm herself down. "And you will sweetheart. Just wait for it. Anywhoo, see you killed one of his best and then you thought you could just walk around and kill even more of our kind? Please." She rested her hands on the right side of the table top I was laying on, waiting for my inevitable witty retort.

"Yellow-eyes had it coming." I said, yanking on my right wrist restraint.

"Maybe. But so do you." The last thing I remember is her picking up an ice pick and a hammer and the blinding pain of my arm being shattered.

….

"Man, she sure fucked you up." Benny commented after one of the guards shoved me back in my cell. Ruby was nice enough to heal all the wounds until she then decided she didn't want me to get off so easy.

After re-shattering my arm, she called a guard to escort me back to my cell.

"Thanks. As if I didn't already know that." I cradled my arm as bursts of pain pulsed through it.

I heard a soft chuckle come from Castiel's cell as he made his way over to his bars to get a better look at me. "I guess she wanted your first day to be memorable."

"Why did she heal me anyways? I mean, why go through hours of torture and then just make it all go away?" I questioned.

"They want us alive, Dean. That way the next day they can start fresh and don't have to worry about us keelin' over. Also, the mental torture is a pain in the ass." Benny explained, resting his arms on the horizontal bars.

Cas laughed again. "You sound like such a pansy."

"So what, are we Hell's most wanted? That's how we got down here?" I asked, Ruby hadn't really explained as much as I hoped so maybe these two would.

"Sure, if you want to put it that way. I set up some cruise deal with some demons only to have it all tank and over 3 hundred of their kind was killed. That's how I got here." The vampire said. He paused for a second and then gestured toward the angel. "Cas here he-"

"It's none of his fucking business." Castiel said, cutting him off.

"That bad, huh? The way I see it, if you fucked over some demons, it's definitely worth sharing." I pressed. Something about Cas's tone made it obvious he didn't want to talk about it, but I gotta say I was damn curious.

Before Cas could respond, the door at the end of the hallway opened again, this time a different demon walked in. This one had medium length dark brown hair.

"That's Meg. If she's here, Ruby must be up top, maybe getting some other poor bastard." Benny clarified.

Opening up the cell next to mine, Meg dragged out a girl with long blonde hair similar to Ruby's.

"Come on sweetheart, your turn." Meg sneered as they continued their way down the hallway.

"Who was that?" I couldn't help but feel sorry for the girl. She looked young but young according to me was mid twenty's.

"Jo Harvelle. Her mom Ellen used to be down here but they accidentally had too much fun while she was being tortured and killed her."

"I'm surprised she hasn't said anything since you arrived. Normally she jumps on any chance to put in her two cents." Castiel chimed in.

I took one last glance down the hallway as the door slammed shut. "How many more people are here?"

"Let's see, Gordon Walker is in the very first cell, Charlie Bradbury is in the one next to Cas." Benny paused, trying to think.

"Don't forget about the cranky guy at the end of Dean's row." Cas added with a chuckle.

"He never talks, we don't even know his name." Benny stated. "I think that might be it. You'll be able to meet all of em later."

"What's later?"

….

"You gotta be fucking kidding me." I said in disbelief. We were all escorted to this big open room, a few tables scattered around.

"Welcome to the compound non-yard." Castiel said with fake excitement. "This is where they send us in hopes we will fight each other so they can watch for their own enjoyment." With a sour smile, Cas made his way over to a bench and pulled out a cigarette, lighting it.

I rolled my eyes as I took in my fellow inmates.

There was a red head talking to Jo at one of the tables. A tall black man, Gordon I think was his name, was leaning against the wall, one foot resting on the wall.

"Where's the cranky guy?" I whispered to Benny who hadn't left my side.

"He doesn't come out here. Lost his privilege." The vamp stated flatly. "Now, watch your back around Gordon. He can be pretty, on edge most of the time."

My eye caught a hand that belonged to the red head waving me over. Benny shot me a sideways glance as I shrugged casually and made my way over to them.

Sitting down next to Jo at the table, I kept my one arm pressed against my body while the other rested on the table. "Welcome to Hell. I'm Charlie." The red head smiled, sticking out her hand for me to shake.

I nodded and shook her hand. "Dean." I answered plainly.

"Jo." The blonde said, sending me a small nod.

"So, any plans on getting out of here?" I asked. I didn't plan on spending a lot of time down here and seeming as though these two were among the only humans here, I figured I should start with them.

Jo let out a small laugh as she looked at me with amusement. "You just get right to business don't cha? Sorry, don't think there's any way out."

"You haven't had my expertise though." I sent Jo a quick wink before I looked at Charlie. Something about her just told me she was the smart one. "What about Cas? I mean, he's an angel right? Can't he like, raise us from perdition?"

"Oh, Cas is kinda off limits with stuff like that. It's a touchy subject. See, he killed a bunch of his own kind and was doing the demons dirty work and then he double-crossed the demons. It's a big confusing mess, really. Not even Hermione could explain it."

"I'm sorry, who?" I asked, my eyebrows furrowed in confusion.

"It's not important. Anyways, if we were to get out, Cas wouldn't be much help." Jo cut in.

Just as I was about to respond, Gordon Walker joined us, sitting across from me.

"Dean Winchester. I'm Gordon." He said, a cruel smiling creeping across his face.

I nodded, giving the strange man a weary look. "I've heard. Can you give us a minute?" I asked. I saw Charlie's eyes widen right before Gordon tackled me to the ground

"What the fuck is the matter with you?" I said exasperated.

"I don't take orders for grunts like you." The maniac said, punching me across the jaw.

Somehow I got my feet up on his chest, kicking him off of me. Benny rushed over, helping me up while Cas shoved Gordon away from me.

The vampire put a harsh hand on my chest when I tried moving towards my attacker.

"If you know what's good for you, you'd walk away." Benny threatened, showing his teeth.

"I'll see you later, Dean. Maybe when your two boyfriends aren't there to protect you." With that, Gordon walked over to one of the guards who had just stood idly by.

I watched as he made his way back to his cell, brushing off my shirt with my good hand. "What a dick." I said as Cas strolled over to Benny and I.

"I guess Benny didn't warn ya. Don't irritate Gordon." Cas said, patting me on the shoulder.

"So does this make you two my bitches?"

….

**TBC**

**Please continue to read and review. Sorry this chapter wasn't very actiony. But next chapter we will meet the cranky guy. Any guesses who it is?**


	4. Chapter 4: Unexpected Allies

**CHAPTER FOUR: Unexpected Allies**

I was lying on my cot, one arm thrown over my eyes, minding my own business, when a tiny rock hit me in the nose.

"What the fuck." Opening my eyes and sitting up, I was greeted with a smiling Benny looking at me from his cell, a glint of mischief in his eyes.

"Morning sleeping beauty." The vampire quipped.

Running a hand through my hair, I got up and stretched. Thankfully, after my second torture session Ruby had decided to heal me completely.

"Hey Dean?" I heard a hushed voice from the cell next to me. Moving as close as I could to the wall, resting my head on the bars, I responded. "Yeah Jo?"

"Remember that whole escape plan idea?" She asked, mimicking my position in her cell.

My interest being peaked, my excitement was evident in my voice. "Yeah, why? Did you have a stroke of genius?"

"I've heard a rumor. Story goes that Meg hates the King as much as we do. Heard she'd do anything to double cross him." She explained, excitement getting the better of her.

I raised an eyebrow as I glanced at Benny and Cas. "Is that so?" I saw some red hair peaking out, indicating Charlie was trying to hear the conversation from her cell next to Castiel's.

"That's what's been going around at least." Jo reminded us.

"And who did you hear this valuable information from?" Castiel said, skeptically.

"The old cranky guy." Jo said slowly. "It doesn't matter who I heard it from. It's reliable."

Benny scoffed as he looked at me. "I wouldn't go off of it if I were you Dean. That guys crazy, been down here too long."

"Hey, you never know, maybe he knows a little about some things." Charlie chimed in.

All four of our gazes turned toward the door when we heard it slowly creak open. Meg walked in, but instead of coming down to our end of the hallway, she stopped at the second cell.

"Speak of the devil…" Castiel said, standing up from his cot and joining the rest of us at his bars.

Seeing the flash of a baseball capped guy being dragged from the cell, my breath caught.

….

"You okay, bud?" Benny questioned, eyeing me suspiciously.

Figuring I was hallucinating, I blinked the image away as I turned my attention to the worried vampire. "Yeah just- just lost in thought I guess." I said distractedly.

All of a sudden all of our cell doors flung open.

As the other prisoners made their way into the hallway, I stopped and stared at Benny wide-eyed.

"It's lunch time." Was all he said before pushing me in front of him, chuckling.

….

As we walked in to the dark cafeteria, I couldn't help but repeat the same phrase I had said about the yard. "You gotta be fucking kidding me."

"Are you going to say that every time you go someplace new?" Castiel said, annoyance in his voice.

"Cool it, Cas. Give him a break. Nobody expects it to be like regular prison." Benny paused a second before leaning closer to me. "Minus the torture of course."

After grabbing a tray of God knows what from the line, I joined the table consisting of Cas, Benny and Charlie.

"Where's Jo?" I asked, sitting next to Charlie, looking around the room. My gaze caught Gordon's from the line and a cruel smile crept across his face. Shaking my head, I turned my gaze on Charlie.

Moving what looked like meatloaf around her plate, she shrugged casually. "It's her turn with Ruby."

A grim silence passed over the table, all of us knowing what she was referring to. Thankfully, we didn't sit like that for long before the door opened, the one prisoner I haven't had the pleasure of meeting yet strolling in.

As I stood up, locking eyes, his face took over a look of absolute shock and then sorrow in two seconds flat.

"Dean?" The man said, hoping it really wasn't me.

"Bobby?"

….

Cas almost choked on his food when he saw Bobby making his way over here, reacting to the name. "You know him?" The angel asked, disbelievingly.

"He's a family friend." I said, absentmindedly as Bobby came over and embraced me, holding me tight.

"It's so good to see you boy." As if hearing what that must've sound like, the old hunter pulled away but kept his hands on my shoulders. "Not like- you know what I mean."

"It's good to see you to Bobby." I smiled sadly at him as he finally let go of me. Finally noticing I wasn't alone, he looked at the people I considered friends.

"Uh, Bobby this is Charlie, Benny, and Cas." I said, gesturing to each. The group mumbled hellos as the old hunter nodded.

I took a second to really look at the man I had started to consider my real father. He had a frantic look in his eyes and they never remained at one spot for long. He had obvious bags underneath his eyes and was sickly pale. He was wearing a worn green t-shirt and torn jeans.

Taking a seat back at the table, Bobby sat across from me next to Cas and Benny. The vampire looking extremely flustered sent a quick glare at me before taking a bite out of his raw meat.

"So," I stopped, giving Benny a disgusted look. "Jo told us that you shared with her that Meg isn't a loyalist."

"Oh she's a loyalist alright, but not to Crowley. She serves Lucifer and that's it. But convincing her to help us escape…" Bobby gave a troubled look, all hope leaving his eyes.

Sending a look of confidence to my tablemates, a banged a fist on the table. "I'm telling you guys, me coming down here will be the best thing that's happened to you people in years. I can recruit Meg."

….

**TBC**

**Thanks so much for all the follows, favorites, and reviews. I hope you are still enjoying the story. Thanks for reading.**


	5. Chapter 5: New Inmate

**CHAPTER FIVE: New Inmate**

It had been three days since Bobby and I reunited and I hadn't had a single chance to talk to Meg yet.

Impatience settling in, I paced my cell.

"Bud, you need to calm down." Benny drawled, eyeing me worriedly.

Walking over to the bars, my eyes were trained on the now opening door and the demon I had been dying to see strolling in.

"Meg." I called, a smirk evident in my tone.

Chuckling slightly, the brunette stopped in front of my cell, crossing her arms. "You rang?"

"I have a question." Resting my arms on the horizontal bars, I beckoned her forward so I could whisper in her ear. "How do you feel about crossing Crowley?"

I felt her lip twitch up in amusement as she moved towards me, her mouth in between the bars, her hot breath tickling my ear. "I'm loyal to my King Dean-o. Nice try though."

Leaning back a bit, I raised an eyebrow at the demon. "Last time I checked Lucifer wasn't the one calling the shots."

Smirking, Meg backed away from my cell and started walking down the hallway. "I'd keep your observations to yourself if I were you, Winchester."

"Real smooth." Cas said sarcastically from his cot.

"Not helping Cas." Grumbling, I plopped down on my own bed just as the lights went out.

….

I was woken up by a hard flick to the ear.

"What the fuck?" My eyes flying open, I groaned as I saw Meg standing over me.

Putting her hand over my mouth, I glared up at her. "We need to talk. But not here. Are you going to be quiet?" Giving her a silent nod, she removed her hand.

Motioning for me to follow her, she made her way to the end of the hallway.

….

It had been five years since Sam had talked to his brother.

Five years of absolute silence.

Except, every year on Sam's birthday he would receive a voicemail from Dean saying happy birthday and anything else that he stammered out.

But for some reason, this year Sam didn't get a shitty voicemail.

Sam had even seen the articles in the paper about the killings and he figured Dean might be around to solve the obvious case. But he didn't stop by.

He waited all day to hear from his brother, tapping his hand with his phone on the front porch of his Alabama home.

"Sam? We're going to be late for our reservation." A woman said from the front doorway, putting in her hoop earrings.

He mentally shook himself, shoving his phone in his pocket. "What? I'm coming Jess. Just… give me a second." Sam glanced over his shoulder to smile at his wife before returning to staring blankly at the road.

_Something's wrong._

…

"Why are we in a closet?" I whispered, harshly as I took in the different rags and bleaches that covered the shelves around me. _Probably for cleaning up any blood spills. _

"Like you're not use to being in the closet." Giving her an agitated look, she put her hands up as if in surrender before going on. "Now, you mentioned fucking over Crowley." Crossing her arms, Meg stared at me expectantly.

"Why? Are you interested?" I questioned, eyeing her suspiciously.

She raised an eyebrow and shrugged.

"Can you get us out of here? All of us?" I felt my heart quicken at the excitement of the possibility of getting out.

Meg furrowed her brow as if in thought. "It'd be pretty damn difficult, especially since I'm not sure when Ruby is going to be back."

I shook my head as I stared at the demon in confusion. "Back? Back from where?"

Meg chewed worriedly at her bottom lip, avoiding eye contact with me. "She went to go pick up someone to bring down here. And she won't want to cross Crowley."

Something about her tone struck me as wrong. It didn't make sense why Meg was so nervous about telling me that bit of information.

"If this is going to work, you need to level with me. What aren't you telling me?" I hissed, tired of being lied to.

"She went to go get your brother."

….

"Sam if you check that phone one more time I might have to break it." Jess teased, her tone light.

Sam smiled apologetically as he returned his attention to look over the menu. Not able to take it anymore, he finally gave in. "I'll be right back."

Not giving his wife a chance to respond, Sam got up from the table abruptly and went outside to make a phone call he should've made years ago.

As the phone continued to ring over and over again, Sam could feel his anxiety levels go through the roof. All these years Dean hadn't missed a birthday and now he won't even pick up the damn phone?

Sam had this pit in his stomach he couldn't get rid of.

"He won't be answering you anytime soon."

Spinning around, Sam pulled out the gun from his waistband that he carried out of habit. "Ruby?"

"Aw, Sam. I'm touched you remember me." As the blonde took a step towards the former hunter, he took a step back.

"Where's Dean?" Sam demanded, hearing his voice rise with anger and worry.

"Downstairs burning. You'll be joining him soon enough." Ruby's words were laced with amusement as she kept walking forward, running Sam into the brick wall behind the restaurant.

"I've missed you, Sam." Placing a rough hand on his chest, Ruby pinned the youngest Winchester up against the wall. "We're going to have so much fun."

With just a flick of her wrist, Ruby sent Sam flying into a dumpster, knocking him unconscious.

….

_No_

"No no no. This can't be happening." I ran frightened hands through my hair as I paced the small space of the closet. "You can't let her!"

"I can't stop her without tipping Crowley or Ruby off. Don't worry. When I get you all out, I'll get Sam out too." Meg tried to reassure me, the words sounding strange coming from a demon.

"Come on, we have to get you back before they notice." With a little shove, Meg and I made our way back to my cell.

….

I never went back to bed after my conversation with Meg. Instead I paced my cell back and forth, causing my fellow inmates around me to stare at me with worry.

"Dean? Care to share what's bothering you?" Jo asked, her voice troubled.

"He's been doing it for hours. Ever since he got back from his thing with Meg." Cas said, irritability tainting her words.

Jo glanced at Benny for an explanation. Sighing heavily, the vampire elaborated. "Meg will help us. But not until after Dean's brother is brought down here by Ruby. That's where Ruby's been."

The whole room went silent as the door opened and my mop-headed brother was being dragged in.

….

**TBC**


	6. Chapter 6: Welcome To Hell

**I've decided to change to a narrative for this chapter (and possibly others) in order to get a good feel for ALL the characters. The next few chapters I'm planning on going into some side stories and it'll be easier if I just do a narrative.**

**CHAPTER SIX: Welcome To Hell**

As Dean stared wide-eyed at his brother, his fellow inmates stared at him with worry.

"Dean?" Jo asked tentatively, her eyebrows creased with concern.

The eldest Winchester couldn't help himself. He had to be positive it was his brother or he'd drive himself crazy. "_SAMMY_."

Sam and Dean made brief eye contact before Ruby shoved the youngest Winchester forcefully into his very own cell right next to Bobby, the door closing with a final clank that echoed against the dark walls.

"Wow, you just seem to know everybody." Cas quipped from his position on his cot.

"Fuck off, Cas." Dean spat, not in the mood to deal with the hormonal angel especially when he saw Ruby sauntering her way towards him.

As she stopped in front of Dean's cell she leaned forward to rest her arms on the horizontal bars, a sense of confidence coming off her in waves. "Are we having fun yet?"

The eldest Winchester banged on the bars, getting as close to Ruby as allowed with his nostrils flaring. Dean's voice dropped dangerously low with a warning in his tone as he spoke. "I swear if you touch him, I'll kill you myself. And trust me when I say this, when I make a promise, I keep it."

As the demon looked in the hatred filled green eyes of the hunter in front of her, Ruby couldn't help but have her sly grin falter a bit as she took a cautious step back. "Will see about that, Winchester." Her voice shook as she tried to respond boldly, falling short.

The inmates all watched as she made her way down the hall and slammed the door shut.

…

Sam barely remembered how he got here, he just remembered Ruby flinging him against a dumpster.

As he regained consciousness, he noticed the demon was dragging him down the hall by his hair.

"What the fuck?" He snarled as he helplessly went with Ruby down the dark hallway. The tall hunter gagged slightly as the smell of burning flesh penetrated his nostrils.

"I'll let your brother explain everything." Ruby purred, obviously happy about the situation, the loud click of heels echoing against the walls.

"Dean's here?" Sam questioned, his anxiety level spiking. "Where am I?" There was a trace of fear in the former hunter's tone as he took in the creepy atmosphere.

The demon reached forward, yanking a door open with her free hand before hauling him inside, his eyes trying to adjust to the dim lighting. "Hell." She answered simply as the door shut behind them firmly.

"_SAMMY_."

At the use of the familiar nickname, the youngest Winchester looked up, immediately making eye contact with none other than his older brother.

Before he could yell out a response, Ruby shoved him inside a musty cell, the door sliding shut with finality.

As Ruby made her way down to the opposite end of the hall, Sam glanced around the cells near him, noting an agitated looking African American man in the cell across from him.

"Sam?" A voice from beside him questioned. Positioning himself as close to the wall separating him and Bobby as possible, he briefly got a glance of a worn baseball cap.

"Bobby?" Sam asked incredulously, not believing the old hunter was down here as well.

"Balls." The man next to him muttered. "Dammit son, not you too."

"Bobby, what's going on?"

….

"It'll be okay Dean." Charlie tried to reassure the distressed hunter who had not stopped his pacing. "Meg has a plan remember?"

Dean ran a tired hand down his face as he stopped, resting his forehead against the cool bars. "I just wish we could get on with it already." He sighed, a trace of desperation in his voice.

Without any warning, all their cell doors opened signaling it was time to go out to the contact non-yard.

Dean tried to catch a glimpse of his brother but there were too many bodies shoving people forward. _Be patient. Just wait two more seconds, _Dean tried to keep up reassuring thoughts as they all made their way to the yard.

….

As Sam confusedly made his way out to the yard, his gaze searched frantically for his older brother. Bobby had stuck relatively close to his side but right now, the youngest Winchester really needed his older brother.

Dean pushed past Cas and Charlie, his eyes landing on his brother who had a lost puppy dog look to him. Approaching him, Sam looked like he was just bursting with questions.

"Hiya Sammy." Dean started but was cut off when the taller man rushed forward to embrace his family member he hadn't seen in years. "Good to see you too, I guess." Dean added awkwardly, not liking the chick flick moment.

"Dude, what the hell?" Sam asked after pulling away. He glanced at the multitude of diverse people that passed them, Gordon sending them a quick glare for standing in the middle of the path. Dean nodded his head towards his group's usual table and Sam followed him over, sitting across from him.

The eldest Winchester cleared his throat, not sure where to start before it just started to flow out of his mouth. The whole time Dean was explaining, Sam had a look of concentration as he took it all in with his eyebrows furrowed. Once the short-haired hunter had finished, Dean really had a chance to look at his little brother.

Sam was dressed in jeans and a nice dress shirt with a gold wedding band on his finger. His hair had grown to just above his shoulders and he had bags just about as deep as Dean's under his eyes.

"Wait, I still don't understand why _I'm _here. I mean, you sure I get." Sam hesitated, sending his brother an apologetic but a 'come on, you know it's true" kind of look before continuing. "But I haven't been hunting in years. Why am I being dragged into this?" Sam was spinning his ring around his finger unconsciously, his worry for Jess occupying his thoughts.

Dean rolled his eyes, ignoring his brother's comment about him basically belonging down there. "I don't know Sam. To get back at us? I mean it's not like our family is completely innocent on the demon spectrum." The eldest Winchester glanced at the ring, a pang of guilt going through him. _I should've prevented this from happening. _

Sam ran a nervous hand through his hair before wiping it down his face. "What the hell are we gonna do?"

"Oh, Dean-o here has a great plan for that." Benny drawled as he plopped down next to his friend. "A stupid plan, but a plan."

Sam glanced at the newcomer warily, before Cas, Jo, Charlie, and Bobby all joined them, filling up the table completely.

As introductions were made, the worry lines on the youngest Winchester's face seem to deepen, not wanting to trust all these people with his and his brother's life.

All gazes turned to the door as Meg walked into the room, her eyes filled with concern as they landed on Dean. "Someone wants to see you."

…

**TBC**

**Please continue to read and review! It means a lot.**


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